The present article describes the synthesis of two novel series of thiosemicarbazones 3 and thiazolylhydrazinomethylidenepyrazoles 5. All the newly synthesized target compounds (3a–e and 5a–o) were screened for their in vivo anti-inflammatory (AI) activity using carrageenaninduced rat paw edema assay and in vitro antibacterial activity against two Gram-positive and two Gram-negative bacteria. Eight compounds (3b–d, 5b, 5e, 5f, 5i, and 5o) showed consistently excellent AI activity (C70% inhibition), at 3 and 4 h after the carrageenan injection, comparable to that of standard drug indomethacin (78%) whereas the remaining twelve compounds have shown significant activity with 57–75% inhibition after 3 h and 56–63% inhibition after 4 h. All the tested compounds showed moderate antibacterial properties.